20168-99-4 Usage
Originator
Cindomet,Chiesi
Manufacturing Process
6.0 g of cinnamoyl chloride was dropwise added to a mixture of 8.7 g of pmethoxyphenylhydrazine hydrochloride, 10.1 g of triethylamine and 200 ml of
toluene under cooling at -5° to 0°C. The reaction mixture was stirred at 20°-
25°C for 1 h. The separated precipitates were filtered off and dry gaseous
hydrogen chloride was introduced into the filtrate. As a result a large amount
of crystals of N1-cinnamoyl-N1-(p-methoxyphenyl)hydrazine hydrochloride
were produced. These crystals were collected by filtration and washed with 20
ml of ether and dried to yield N1-cinnamoyl-N1-(p-methoxyphenyl)hydrazine
hydrochloride of melting point 183°-185°C.
A mixture of N1-cinnamoyl-N1-(p-methoxyphenyl)hydrazine hydrochloride andacetonylmalonic acid was heated in acetic acid at heating with stirring.
Thereafter, the reaction mixture was allowed to cool, and was poured into cold
water, and then crystals were produced. They were collected by filtration, and
dried to give crude product. The recrystallization from acetone-water gave fine
white needle crystals of 1-cinnamoyl-2-methyl-5-methoxy-3-indolylacetic acid,
melting point 164°-165°C.
Therapeutic Function
Antiinflammatory
Check Digit Verification of cas no
The CAS Registry Mumber 20168-99-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,1,6 and 8 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 20168-99:
(7*2)+(6*0)+(5*1)+(4*6)+(3*8)+(2*9)+(1*9)=94
94 % 10 = 4
So 20168-99-4 is a valid CAS Registry Number.
InChI:InChI=1/C21H19NO4/c1-14-17(13-21(24)25)18-12-16(26-2)9-10-19(18)22(14)20(23)11-8-15-6-4-3-5-7-15/h3-12H,13H2,1-2H3,(H,24,25)/b11-8+
20168-99-4Relevant articles and documents
Anti inflammatory activities of 1 cinnamoyl 2 methyl 5 methoxy 3 indolylacetic acid (cinmetacin)
Komatsu,Saito,Awata,Sakai,Inukai
, p. 1690 - 1696 (2007/10/08)
1 Cinnamoyl 2 methyl 5 methoxy 3 indolylacetic acid (cinmetacin, Indolacin), an indolylacetic acid derivative, is a new potent antiinflammatory agent with low toxicity. The antiinflammatory activities are more potent than those of oxyphenbutazone, but are considered to be about 1/4 that of indometacin on acute inflammation models. Cinmetacin, further, exhibits marked effects on chronic inflammation models (about 1/20 of indometacin). In addition, the significant analgesic and antipyretic effects equivalent to about 1/2 those of indometacin are exhibited. The most characteristic property of cinmetacin is its being markedly less toxic than indometacin. Considering from LD50 or ulcerogenic effects in rats, the present compound is 20 to 30 times more tolerable than indometacin. When therapeutic indices (ED50 in ulcerogenic effect/ED50 in carrageenin edema test) are calculated, it is concluded that cinmetacin is about 5 times safer then indometacin or oxyphenbutazone.
